Cesium carbonate → HCID 118863107, compound

HRID 63918Notes

Reaction equation

HRID 63918 reaction equation
Br[CH2:2][C:3]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8](=[O:20])[N:7]([CH3:21])[C:6]=2[S:5][C:4]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=1.[Cl:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1>[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:2][C:3]2[C:11]3[C:10](=[O:12])[N:9]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8](=[O:20])[N:7]([CH3:21])[C:6]=3[S:5][C:4]=2[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 742994-Chlorophenylboronic acidHCID 118863113ethyl 3-(5-(bromomethyl)-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate

Product 1

HCID 118863107HCID 118863107, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 3-(5-(bromomethyl)-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (100 mg, 0.187 mmol) in toluene (5 mL) was added (4-chlorophenyl)boronic acid (32.1 mg, 0.205 mmol) and aq. Cs2CO3 (1 M, 0.28 mL). The reaction was degassed under nitrogen gas (3×) then Pd(PPh3)4 (10 mg) was added. The reaction was heated at 100° C. for 18 h, cooled to RT then diluted with EA (10 mL). The organic layer was washed with brine (5 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (4:1 to 2:1) to give ethyl 3-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (51 mg, 48.1% yield) as a yellow solid. LCMS: MH+ 567 and TR=1.710 min.

Workup

  1. customThe reaction was degassed under nitrogen gas (3×)
  2. additionPd(PPh3)4 (10 mg) was added
  3. temperaturecooled to RT
  4. additionthen diluted with EA (10 mL)
  5. washThe organic layer was washed with brine (5 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to a residue which
  8. customwas purified by chromatography
  9. washeluted with PE/EA (4:1 to 2:1)

Sources & evidence

ORD record
ord-33aa31b1adae460c8528ef72cb0b79b6
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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